JP2005187351A - Anti-microbial agent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an anti-microbial agent which has an excellent anti-microbial activity against a wide range of microorganisms and is safe for human bodies. <P>SOLUTION: This anti-microbial agent comprises 2,2-dimethyl-1-phenyl-1,3-propanediol represented by formula (1). <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

The present invention relates to an antibacterial agent. More specifically, the present invention relates to an antibacterial agent that has excellent antibacterial activity against a wide range of microorganisms that can be preferably used in a composition for external use on skin, a cleaning material, food, daily necessities, etc., and is safe for the human body.

In order to suppress the growth of microorganisms, sorbic acid, dehydroacetic acid and its salts, paraoxybenzoic acid derivatives, etc. are often used as antibacterial and antiseptic agents for foods, pharmaceuticals, cosmetics, etc. There is a problem, and the amount of addition and target food are limited (for example, the upper limit of incorporation of sorbic acid and its salt into food is 0.2%, dehydroacetic acid and its salt can be used only for cheese, butter and margarine In addition, the upper limit of incorporation of methyl sodium paraoxybenzoate into cosmetics was 1.0%).

In order to suppress the growth of microorganisms, in the living body, the invasion of microorganisms is suppressed by chemical methods such as physical or bactericidal substances and mucus distribution in the skin and mucous membranes. For example, resistance is achieved by innate and nonspecific infection resistance, immune response to specific pathogens, such as adhesion prevention by immunoglobulin, phagocytosis by phagocytic cells, and lysis by lysozyme.

However, if the infectivity of microorganisms exceeds the resistance in the living body, in vivo, for example, infectious dermatitis such as pyoderma caused by Staphylococcus aureus, food poisoning, sepsis, conjunctivitis due to Bacillus subtilis, iritis Urinary tract infections due to Escherichia coli, diarrhea, periodontal disease due to Actinobacillus, caries due to protozoa, acne (propionibacteria acnes), dandruff (Pityrosporum obare) There is a risk of causing various infectious diseases such as acne, dandruff or scabs accompanying dandruff.

Therefore, various drugs have been used for the prevention and treatment of infectious diseases both inside and outside the body. Antibiotics, antibacterials and antiseptics, which account for the majority of these drugs, have a strong effect, but are safe. There is a problem in terms of sexuality, and strict attention is required for their use, and more useful substances have been demanded in terms of efficacy and safety.
Therefore, the present inventors have antibacterial and antiseptic effects against infectious diseases and diseases caused by microorganisms such as bacteria, yeasts, and molds, that is, have effects of sterilization or prevention of reproduction over time, and are used in various fields. However, I have been eagerly researching what is safe.

An object of the present invention is to provide an antibacterial agent that has excellent antibacterial activity against a wide range of microorganisms and is safe for the human body.

In view of the above problems, the present inventors have shown that 2,2-dimethyl-1-phenyl-1,3-propanediol represented by the following chemical formula (1) has a strong antibacterial and antiseptic effect against various microorganisms. The present inventors have confirmed that it is safe for humans and animals, discovered that it is very effective to be applied to various fields as a novel antibacterial agent, and completed the present invention.

That is, the present invention is an antibacterial agent comprising 2,2-dimethyl-1-phenyl-1,3-propanediol represented by the following chemical formula (1).

Hereinafter, the configuration of the present invention will be described in detail.

2,2-dimethyl-1-phenyl-1,3-propanediol represented by the following chemical formula (1) used in the present invention is a known substance, but is a novel use as an antibacterial agent.

2,2-Dimethyl-1-phenyl-1,3-propanediol used in the present invention can be produced by a general synthesis method. For example, it can be easily produced from benzaldehyde and isobutyraldehyde. (For example, it can be obtained by the method of Wolter ten Hoeve et al. (J. Org. Chem. 1985, 50, 4508-4514).) In addition, 2,2-dimethyl-1-phenyl-1,3-propanediol is obtained from Aldrich. Etc., and are easily available.

The 2,2-dimethyl-1-phenyl-1,3-propanediol used in the present invention may be an optically active substance, a racemate, or a mixture thereof.

  The antibacterial agent of this invention can be mix | blended with arbitrary skin external compositions. Further, the antibacterial agent of the present invention is a medical cleaning agent for disinfecting and cleaning medical instruments and affected parts; a household cleaning agent for sterilizing and cleaning dishes; a food industry cleaning agent; a food packaging film, a fiber, and a synthetic resin Antibacterial agent for antibacterial processing of wood, daily necessities, etc .; antibacterial paint; marine products such as oral compositions (gum, candy, etc.), kamaboko, chikuwa, livestock products such as sausage, ham, confectionery, noodles Also, it can be blended as a seasoning such as sauce and soy sauce, an antibacterial agent for food such as side dishes and beverages, and the like.

  The usage method of the antibacterial agent of this invention is not specifically limited, It can apply to various object. For example, methods usually employed such as a method of adding to an object, a spraying method, a coating method, a dipping method, an impregnation method, and a kneading method at the time of molding can be used as they are.

  The antibacterial agent of the present invention can be used as it is, but the blending amount when blended as an antibacterial agent varies depending on the product form and the degree of expected action and is not particularly limited, but is usually 100 ppm or more, preferably 1000 ppm or more. Is good.

In addition, when the 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention is blended in various compositions, food, cosmetics, pharmaceuticals, and pharmaceutical departments are within the range not impairing the effects of the present invention. Various ingredients commonly used in external products, such as sugar, condensed milk, flour, shortening, salt, glucose, chicken eggs, butter, margarine, chickenpox, calcium, iron, seasonings, spices and oils (animal and vegetable oils, mineral oils) , Ester oils, wax oils, silicone oils, higher alcohols, phospholipids, fatty acids, etc.), surfactants (anionic, cationic, amphoteric or nonionic surfactants), vitamins (vitamin A group, vitamins) B group, folic acid, nicotinic acid, pantothenic acid, biotin, vitamin C group, vitamin D group, vitamin E group, other ferulic acid, γ-oryzanol, etc.), External absorption agent (p-aminobenzoic acid, anthranyl, salicylic acid, coumarin, benzotriazole, tetrazole, imidazoline, pyrimidine, dioxane, furan, pyrone, camphor, nucleic acid, allantoin and derivatives thereof, amino acid compound, shikonin, baicalin, Baicalein, berberine, etc.), antioxidants (stearic acid ester, nordihydrogua seltenic acid, dibutylhydroxytoluene, butylhydroxyanisole, parahydroxyanisole, propyl gallate, sesamol, sesamolin, gossypol, etc.), thickener (hydride) Xylethylcellulose, ethylcellulose, carboxyethylcellulose, methylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, hydroxypropylcellulose , Nitrocellulose, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, polyvinyl methacrylate, polyacrylate, carboxyvinyl polymer, gum arabic, tragacanth gum, agar, casein, dextrin, gelatin, pectin, starch, alginic acid and salts thereof) , Moisturizer (propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycerin, 1,2-pentanediol, hexylene glycol, octylene glycol, chondroitin sulfate and its salt, hyaluronic acid and its salt, sodium lactate, etc.) In addition, lower alcohols, polyhydric alcohols, water-soluble polymers, pH adjusters, antiseptic / antifungal agents, coloring agents, fragrances, refreshing agents, stabilizers, animal / plant extracts, animal / plant proteins, Degradation products, animal / plant polysaccharides and degradation products thereof, animal / plant glycoproteins and degradation products thereof, microbial culture metabolic components, blood flow promoters, anti-inflammatory agents, anti-inflammatory agents, anti-allergic agents, cell activators , Amino acids and salts thereof, keratolytic agents, astringents, wound healing agents, foaming agents, oral preparations, deodorizing / deodorizing agents, emulsifiers and the like, and can be used in combination.

In addition, the dosage form when the 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention is blended into the composition for external use of the skin is arbitrary, and blended by a conventional method, for example, lotion , Cream, ointment, emulsion, foundation, oil, pack, soap (including medicated soap), body soap, lipstick, nail cosmetics, eyebrow cosmetics, perfume, face wash, oral products (toothpaste, mouthwash, etc.), deodorant (Smell, foot odor, etc.), bath preparation, shampoo, rinse, hair tonic, hair spray, hair dye, etc.

Further, the dosage form when the 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention is blended with other compositions is also arbitrary, blended by a conventional method, for example, an oral drug , Textile products (sheets, clothing, etc.), sanitary cotton, wet tissue, wiping paper, non-woven fabrics such as sanitizing cloth, and oral compositions (gum, candy, etc.), kamaboko, chikuwa, etc. Fishery products, sausages, ham and other livestock products, Western confectionery, Japanese confectionery, Chinese noodles, udon, buckwheat noodles, sauces, soy sauce, condiments such as sauce, side dish, juice, soup It can be made into the dosage form.

Furthermore, the form of various compositions containing 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention is arbitrary, and is in the form of a solution, cream, paste, gel, gel, It can be used as foam, solid or powder.

The 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention has an excellent antibacterial activity against a wide range of microorganisms, and can provide an antibacterial agent that is safe for the human body.

Next, the present invention will be described more specifically with reference to examples. The present invention is not limited thereby. A compounding quantity is the mass%.

Test Example 1: Antibacterial effect The minimum inhibitory concentration (MIC) for various bacteria was determined. The following tests were conducted on 2,2-dimethyl-1-phenyl-1,3-propanediol and methyl paraoxybenzoate.
According to the agar plate method, the bacteria are inoculated with the following bacteria in a soy bean casein digest agar medium (Eiken) containing each test compound at each concentration, and cultured at 30 ° C. for 24 hours, and no colony is formed. The concentration (minimum growth inhibitory concentration: MIC) was determined. As for fungi, potato dextrose agar medium containing each test compound at various concentrations was inoculated with the following fungi, cultured at 25 ° C. for 48 hours, and the concentration of each test compound that did not form colonies (minimum growth inhibitory concentration: MIC). ) The determination results are shown in Table 1 according to the following evaluation criteria.
(Test bacteria)
Ps: Pseudomonas aeruginosa standard strain (strain name: Pseudomonas aeruginosa ATCC15442)
E: E. coli standard strain (Strain name: Escherichia coli ATCC8739)
S: Staphylococcus aureus standard strain (strain name: Staphylococcus aureus ATCC6538)
Can: Candida albicans standard strain (strain name: Candida albicans ATCC10231)
Asp: black mold standard strain (strain name: Aspergillus niger ATCC16404)

(Evaluation criteria)
A: Minimum growth inhibition concentration is less than 1000 ppm B: Minimum growth inhibition concentration is 1000 ppm or more and less than 5000 ppm C: Minimum growth inhibition concentration is 5000 ppm or more and less than 10,000 ppm D: Minimum growth inhibition concentration is 10000 ppm or more and less than 30000 ppm E: Minimum growth inhibitory concentration is 30000ppm or more

Test Example 2: Safety Test A safety test was conducted on 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention. As a result of a single-dose toxicity test, the toxicity was judged to be extremely weak. As a result of skin primary irritation test and continuous skin irritation test, skin irritation was determined to be extremely weak. Furthermore, skin sensitization test and genotoxicity test were negative.

As described above, the safety of 2,2-dimethyl-1-phenyl-1,3-propanediol of the present invention was good.

Hereinafter, the method of using the present invention will be described in more detail, but the present invention is not limited to the following examples, and various pharmaceuticals, quasi drugs, compositions for external use in the cosmetics field, cleaning agents, It can be used in foods and daily necessities. In addition, each Example may be what was manufactured by the conventional method in manufacture of each product, and showed only the compounding quantity.

Example 1 lotion mass%
Ethanol 5.0
1,3-butylene glycol 6.0
Glycerin 4.0
Oleyl alcohol 0.1
POE (20) sorbitan monolaurate 0.5
POE (15) lauryl ether 0.5
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.3
Perfume Appropriate amount of purified water

Example 2 lotion
Ethanol 5.0
1,3-butylene glycol 6.0
Glycerin 5.0
Oleyl alcohol 0.1
Ethylhexanediol 0.3
2,2-diethyl-1,3-propanediol 0.3
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.2
POE (20) sorbitan monolaurate 0.5
POE (15) lauryl ether 0.5
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.2
3-Benzyloxy-1,2-propanediol 0.3
3-phenoxy-1,2-propanediol 0.2
3-Hexin-2,5-diol 0.1
Phenoxyethanol 0.2
Methylparaben 0.1
Perfume Appropriate amount of purified water

Example 3 lotion
Sorbit 4.0
1,3-butylene glycol 6.0
Glycerin 2.0
POE (20) oleyl alcohol ether 0.5
Methylcellulose 0.2
Quince Seed 0.1
2,2-diethyl-1,3-propanediol 0.1
Ethylhexanediol 0.3
2,2,4-Trimethyl-1,3-pentanediol 0.2
2,2-dimethylolpentane 0.2
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.2
3-Benzyloxy-1,2-propanediol 0.3
3-phenoxy-1,2-propanediol 0.2
3-Hexin-2,5-diol 0.1
Phenoxyethanol 0.2
Methylparaben 0.2
Perfume appropriate amount purified water

Example 4 Latex mass%
2,2-Dimethyl-1-phenyl-1,3-propanediol 2.0
Glycerin 3.0
2,2-diethyl-1,3-propanediol 0.2
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.5
Ethylhexanediol 1.0
Cetanol 1.5
Stearyl alcohol 1.8
Dimethylpolysiloxane (20cs) 1.5
Squalane 2.0
Vaseline 2.0
Isopropyl myristate 2.5
Glyceryl monostearate 1.8
Polyoxyethylene (POE = 5) glyceryl monostearate 1.8
Polyoxyethylene (POE = 20) cetyl ether 1.5
Carboxyvinyl polymer 0.25
Potassium hydroxide 0.05
L-Arginine 0.2
Dipropylene glycol 5.0
1,3-butylene glycol 3.0
Edetate trisodium 0.2
3-Benzyloxy-1,2-propanediol 0.2
3-phenoxy-1,2-propanediol 0.1
3-Hexin-2,5-diol 0.1
Phenoxyethanol 0.1
Methylparaben 0.01
Purified water remaining

Example 5 Cream Mass%
2,2-Dimethyl-1-phenyl-1,3-propanediol 1.0
3-Benzyloxy-1,2-propanediol 0.2
3-phenoxy-1,2-propanediol 0.1
2,2-diethyl-1,3-propanediol 0.2
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.5
Ethylhexanediol 1.0
3-Hexin-2,5-diol 0.1
Stearyl alcohol 3.5
Stearic acid 2.0
Squalane 10.5
Isopropyl myristate 7.5
Polyoxyethylene (POE = 25) cetyl alcohol ether 3.0
Glycerol monostearate 2.0
Tocopherol acetate 0.2
Monoammonium glycyrrhizinate 0.05
Glycerin 3.0
Dipropylene glycol 5.0
1,3-butylene glycol 3.0
Phenoxyethanol 0.2
Edetate trisodium 0.01
Ethylparaben 0.1
Purified water remaining

Example 6 Face wash
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.5
3-Benzyloxy-1,2-propanediol 0.2
3-phenoxy-1,2-propanediol 0.1
2,2-diethyl-1,3-propanediol 0.2
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.5
Ethylhexanediol 0.1
3-Hexin-2,5-diol 0.1
Stearic acid 8.0
Palmitic acid 6.0
Myristic acid 6.0
Lauric acid 4.0
Potassium hydroxide 5.2
Glyceryl monostearate 2.0
Propylene glycol 1.0
Bees wax 1.5
Polyethylene glycol 1500 5.0
Glycerin 10.0
Methylparaben 0.01
Phenoxyethanol 0.1
Purified water remaining

Example 7 Shampoo Mass%
Lauryl polyoxyethylene (3) sulfate sodium salt (30% aqueous solution) 25.0
Lauryl sulfate sodium salt (30% aqueous solution) 8.0
Palm oil fatty acid diethylolamide 4.0
Isoprene glycol 4.0
Sodium benzoate 0.5
Dipropylene glycol 1.0
1,3-butylene glycol 1.0
Edetate trisodium 0.01
3-Benzyloxy-1,2-propanediol 0.1
3-phenoxy-1,2-propanediol 0.1
2,2-diethyl-1,3-propanediol 0.2
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.5
Ethylhexanediol 0.1
3-Hexin-2,5-diol 0.1
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.1
Pigment Appropriate amount of flavoring

Example 8 Jelly Pack Mass%
3-Benzyloxy-1,2-propanediol 0.05
3-phenoxy-1,2-propanediol 0.1
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.1
Polyoxyethylene oleyl alcohol ether 0.5
2,2-diethyl-1,3-propanediol 0.1
Ethylhexanediol 0.1
2,2,4-Trimethyl-1,3-propanediol 0.1
2,2-dimethylolpentane 0.1
3-Hexin-2,5-diol 0.1
Monoammonium glycyrrhizinate 0.05
Carboxymethylcellulose 5.0
Ethanol 12.0
Polyvinyl alcohol 12.0
1,3-butylene glycol 5.0
Edetate trisodium 0.01
Purified water balance

Example 9 Eyeliner Mass%
2,2-Dimethyl-1-phenyl-1,3-propanediol 1.0
3-Benzyloxy-1,2-propanediol 0.2
3-phenoxy-1,2-propanediol 0.5
Iron oxide (black) 14.0
Isopropyl myristate 1.5
Polyoxyethylene sorbitan monooleate 1.0
Vinyl acetate resin emulsion 45.0
Monoammonium glycyrrhizinate 0.05
Carboxyvinyl polymer 1.5
Acetyltributyl citrate 1.0
Dipropylene glycol 4.0
Isopropyl alcohol 1.0
Ethylhexanediol 1.0
2,2-diethyl-1,3-pentanediol 1.0
2,2-Dimethyl-1,3-pentanediol 1.0
2,2,4-trimethyl-1,3-pentanediol 0.5
2,2-dimethylolpentane 0.5
1,2-pentanediol 3.0
3-Hexin-2,5-diol 0.1
Phenoxyethanol 0.1
Methylparaben 0.02
Edetate trisodium 0.01
Purified water remaining

Example 10 Hair tonic mass%
Hardened castor oil ethylene oxide (40 mol) adduct 2.0
Ethanol 60.0
Perfume proper amount 2,2-dimethyl-1-phenyl-1,3-propanediol 0.01
Purified water balance

Example 11 Bath agent mass%
Sodium bicarbonate 64.5
Anhydrous sodium sulfate 35.0
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.5

Example 12 Chinese noodles by mass
Wheat flour 98.0
Salt 1.0
Sweetener 0.5
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.5

Example 13 Mentsuyu Solution Mass%
Soy sauce 80.7
Vinegar 1.0
Glucose 15.0
Sodium glutamate 2.0
Sugar 1.0
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.3

Example 14 Buckwheat mass%
Buckwheat flour 96.0
Salt 0.9
Water 3.0
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.1

Example 15 Bread Mass%
Flour 90.0
Salt 1.2
Sugar 2.0
Water 6.5
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.3

Example 15 Ham Mass%
Minced meat 95.0
Egg 4.0
Salt 0.5
Spice 0.4
2,2-Dimethyl-1-phenyl-1,3-propanediol 0.1

Example 16 Fruit juice mass%
Glucose liquid sugar 13.0
Orange juice 85.0
Fragrance 1.0
2,2-Dimethyl-1-phenyl-1,3-propanediol 1.0

All of the above examples showed good antiseptic properties.

INDUSTRIAL APPLICABILITY The present invention can be used for various skin external compositions in the pharmaceutical, quasi-drug, and cosmetic fields (including various preparations used for humans and other animals). Specifically, lotions, emulsions, creams (ointments) ), Sunscreen, foundation, oil, pack, soap (including medicated soap), body soap, lipstick, nail cosmetics, eyebrow cosmetics, perfume, face wash, oral products (toothpaste, mouthwash, etc.), deodorant (Smell, foot odor, etc.), bath preparation, shampoo, rinse, hair tonic, hair spray, hair dye, etc. In addition, it can be applied to medical cleaning materials for the purpose of disinfecting and cleaning medical instruments and affected areas, household cleaning materials for sterilizing and cleaning dishes, and food industry cleaning materials. In addition, textile products (sheets, clothing, etc.), food packaging films, synthetic resins, wood, daily products, antibacterial processing, various forms of oral drugs, sanitary cotton, wet tissue, wipes, sanitizing cloth, etc. Non-woven fabric, marine products such as oral composition (gum, candy, etc.), kamaboko, chikuwa, livestock products such as sausage, ham, Western confectionery, Japanese confectionery, raw noodles, boiled noodles, Chinese noodles, udon, soba , Spaghetti and other noodles, soy sauce, sauces, sauces and other seasonings, side dishes, juices, soups, etc.

Claims (1)

An antibacterial agent comprising 2,2-dimethyl-1-phenyl-1,3-propanediol represented by the following chemical formula (1).